This invention relates to a new class or organosilicon compounds. More particularly, this invention relates to novel functionally substituted phenoxyalkyl-, thiophenoxyalkyl- and pyridyloxyalkylsilanes and to a method for preparing these compounds. The method is applicable to the preparation of known phenoxyalkylsilanes.
The novel compounds of this invention exhibit the general formula ##STR1## wherein R.sup.1 is --NH.sub.2, --NR.sup.8 H, --NR.sub.2.sup.8, ##STR2## --CHO, --CN, --COR.sup.8, --COOR.sup.8, Cl, Br, I, ##STR3## SO.sub.2 R.sup.8, --SOR.sup.8 and --NO.sub.2 ; R.sup.2 is alkyl, alkoxy or thioalkoxy and contains from 1 to 12 carbon atoms; R.sup.3 is Cl, Br, I, --COOR.sup.8, --CN, --NH.sub.2, --NR.sup.8 H, --NR.sub.2.sup.8, ##STR4## R.sup.4 is alkyl containing from 1 to 12 carbon atoms; R.sup.5 is methylene or alkylene containing from 3 to 12 carbon atoms; R.sup.6 and R.sup.7 are individually selected from the group consisting of alkyl, cyanoalkyl, alkenyl, cycloalkyl, aryl, alkaryl and aralkyl, wherein any alkyl group present as all or part of R.sup.6 and R.sup.7 contains from 1 to 12 carbon atoms; R.sup.8 and R.sup.10 are individually selected from the group consisting of alkyl, cycloalkyl, aryl, alkaryl and aralkyl wherein any alkyl group contains from 1 to 12 carbon atoms; R.sup.9 is ##STR5## wherein R.sup.11 and R.sup.13 are individually selected from the group consisting of hydrogen, chlorine, bromine, iodine and alkyl containing from 1 to 12 carbon atoms; R.sup.12 and R.sup.14 are individually selected from the group consisting of hydrogen and alkyl containing from 1 to 12 carbon atoms; Z is oxygen, sulfur, ##STR6## m is an integer from 1 to 5, inclusive; n is 0, 1 or 2, p is 2 or 3, q is 1, 2 or 3 and t is 0 or 1, with the proviso that (a) when m is 2, one or both of R.sup.1 are --NH.sub.2, --NR.sup.8 H, --NR.sub.2.sup.8, ##STR7## or --COOR.sup.8 and any remaining R.sup.1 is --CN, Cl, Br, I or --NO.sub.2 ; (b) when m is 3 one of R.sup.1 is --NH.sub.2, NR.sup.8 H, --NR.sub.2.sup.8, or ##STR8## and the remaining two R.sup.1 groups are chlorine, bromine or iodine; (c) when m is 4 or 5, R.sup.1 is chlorine, bromine or iodine; (d) n is 1 or 2 when m is 1 and R.sup.1 is --NH.sub.2, --NO.sub.2, chlorine, bromine or iodine; and (e) the sum of m and n is equal to or less than 5.
This invention also provides a method for preparing the aforementioned novel compounds in addition to known phenoxyalkyl- and thiophenoxyalkyl silanes, said method consisting of reacting a haloalkylsilane of the general formula ##STR9## with an anhydrous alkali- or alkaline earth metal phenoxide or thiophenoxide of the formula ##STR10## or an anhydrous alkali- or alkaline earth metal salt of a hydroxy- or mercaptopyridine of the formula ##STR11## at a temperature of from ambient to 200.degree. C. under an inert atmosphere and in the presence of a liquid reaction medium consisting essentially of at least one dipolar, aprotic liquid, and, optionally, at least one liquid hydrocarbon boiling from 40.degree. to 200.degree. C. under ambient pressure, maintaining the resultant reaction mixture at a temperature of from 40.degree. to 200.degree. C. for a period of time sufficient to form the desired silane and isolating the silane from said reaction mixture. The present method is applicable to the preparation of known silanes containing functional groups, including the aminophenoxypropyl silanes disclosed in U.S. Pat. No. 4,049,691, the pertinent portions of which are hereby incorporated by reference.